Tributylamine → HCID 87217801, compound

HRID 1434477Notes

Reaction equation

HRID 1434477 reaction equation
[CH2:1]([N:5](CCCC)CCCC)[CH2:2]CC.[CH:14]1[CH:19]=[C:18]2[CH:20]([CH2:27][O:28]C(NCC(O)=O)=O)[C:21]3[C:26]([C:17]2=[CH:16][CH:15]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3.ClC(OCC(C)C)=[O:38].[NH2:44][C@H:45]1[CH2:68][CH2:67][C@@:66]2([CH3:69])[C@H:47]([CH2:48][CH2:49][C@@H:50]3[C@@H:65]2[CH2:64][C:63](=[O:70])[C@@:62]2([CH3:71])[C@H:51]3[CH2:52][CH2:53][C@@H:54]2[C@H:55]([CH3:61])[CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:46]1>C1COCC1.CN(C=O)C>[CH:22]1[C:21]2[CH:20]([CH2:27][O:28][NH:5][CH2:1][C:2]([NH:44][C@H:45]3[CH2:68][CH2:67][C@@:66]4([CH3:69])[C@H:47]([CH2:48][CH2:49][C@@H:50]5[C@@H:65]4[CH2:64][C:63](=[O:70])[C@@:62]4([CH3:71])[C@H:51]5[CH2:52][CH2:53][C@@H:54]4[C@H:55]([CH3:61])[CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:46]3)=[O:38])[C:18]3[C:17](=[CH:16][CH:15]=[CH:14][CH:19]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7622Tributylamine2×HCID 62365Isobutyl chloroformateHCID 93124Fmoc-Gly-OHHCID 23391052HCID 23391052, compound

Product 1

HCID 87217801HCID 87217801, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tributylamine (0.7 mL; 3.1 mmol) was added dropwise to a solution of N-α-Fmoc-glycine (0.9 g; 3.1 mmol) in THF (25 mL) stirred at 0° C. Isobutyl chloroformate (0.4 mL; 3.1 mmol) was subsequently added and, after 10 min, a suspension of tributylamine (0.6 mL; 2.6 mmol) and (3β,5β)-3-amino-12-oxocholan-24-oic acid B (1.0 g; 2.6 mmol) in DMF (30 mL) was added dropwise, over 1 h, into the cooled solution. The mixture was allowed to warm up and after 6 h the solution was concentrated to 40 mL, then H2O (50 mL) and 1 N HCl (10 mL) were added (final pH: 1.5). The precipitated solid was filtered, washed with H2O (2×50 mL), vacuum dried and purified by flash chromatography to give C as a white solid (1.1 g; 1.7 mmol). Yield 66%.

Workup

  1. additionwas added dropwise, over 1 h, into the cooled solution
  2. temperatureto warm up and after 6 h the solution
  3. concentrationwas concentrated to 40 mL
  4. additionH2O (50 mL) and 1 N HCl (10 mL) were added (final pH: 1.5)
  5. filtrationThe precipitated solid was filtered
  6. washwashed with H2O (2×50 mL), vacuum
  7. customdried
  8. custompurified by flash chromatography
  9. customto give C as a white solid (1.1 g; 1.7 mmol)

Sources & evidence

ORD record
ord-4c48e788db4f4cd98c4178ff67511586
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

Loading…